


Bottom's Up Kink-tober

by Always_Bottom_Derek



Category: Teen Wolf (TV)
Genre: Always Bottom Derek Hale, Anal Plug, Begging, Costumes, Face-Sitting, Fisting, Foot Fetish, Inflation, Kink-tober, Licking, M/M, Masks, Medical Play, Mind Control, Oh- and I have used the word rectum twice, Pet Play, Pony Play, Rape/Non-con Elements, Rimming, Sado/Masochism, Spanking, Spells & Enchantments, Underwear Fetish, Watersports, ass worship, deep-throating, feederism, huge ass, huge cocks, sadism/masochism
Language: English
Status: In-Progress
Published: 2018-10-04
Updated: 2018-11-05
Packaged: 2019-07-25 01:10:40
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 4
Words: 11,871
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16186955
Author URL: https://archiveofourown.org/users/Always_Bottom_Derek/pseuds/Always_Bottom_Derek
Summary: My first attempt at this yearly porn ritual. Drabbles done for Kink-tober's daily prompts.Most of these are done in just a few hours, so don't expect masterpieces here, people. Just a filthy, fun, fast fucks.





	1. Oct 1 - Deep-Throating | Inflation | Face-Sitting | Masks

**Author's Note:**

  * For [IcyCryos](https://archiveofourown.org/users/IcyCryos/gifts).



> Come up my cobbled walkway. Red porch light on. Pretty Derek doppelgangers posed in the windows. Ring the bell and hear the sounds of men and women cumming for its chimes.
> 
> "Trick or Treat!"
> 
> *holds out bowl of condoms and glitter wrapped bite-sized bits of porn.*
> 
> "Enjoy, my little costumed darlings!"

Oct 1 - Deep-Throating | Inflation | Face-Sitting | Masks

 

Derek lies on his back on a padded table, his wrists and ankles rope-bound to the heavy, straight metal bar suspended above him.

Just to tease, John gives the inflatable plug in Derek’s ass a couple additional pumps. It makes Derek gasp and pulls tears into his eyes, his rectum already stretched to its aching limits. Right when he's worried he’s going to start crying for real, John relents. The plug deflates.

The emptiness he feels when it’s pulled equals in intensity the previous moment’s ache.

After filling Dere’s ass with additional lube, John gives the straps a final check before moving around by his head. He asks Derek if he's ready before he bends down and kisses him.

It’s Derek’s first amateur porn shoot and it's going to be a dandy.

Then he wipes away Derek's tears and pulls the mask over Derek's face. It’s black and shaped like the Lone Ranger’s, only there are no eyeholes. So when it slips down it plunges Derek into darkness.

With Derek blinded, John travels back down again to suck his cock until he orgasms. It doesn't take long since he was hard and leaking the moment the first coil tightened around one of his muscular limbs. Derek wants to be spent and empty so, when his ass is fucked by 30 strangers tonight, there's nothing to distract him from feeling every thrust. Just an object to be used, his own dick left forgotten.

Coming on cock if he comes at all.

John comes back around after Derek cums for one final kiss. But it's not so much a tradtional kiss, instead he drools Derek’s spend back into his lover’s open mouth.Then he sinks his own cock deep in Derek's throat. Fucking it until he comes. Because John doesn't want to be distracted while he's manning the cameras.

Derek's greedy maw is left cum-frothed and sloppy before the first visitor arrives.

After John cums, he leaves Derek there, alone. Lover’s flavor on his tongue. Waiting. Made to quiver with anticipation while he hears the repeated knocks on the door. Its openings and closings.

Laughter and rough voices as the room slowly fills with his forthcoming fuckers.

He spends the next three hours in a blur of blind sensation. So many raw cocks in his ass. In his throat. Asses ground against his face, threatening to cut off his breath, as his head hangs over the edge of the padded table he's on.

He’s called so many filthy names and he loves it. Is ordered to lick hairy taints and suckle ripe assholes. To swallow cock and worship fat fuzzy balls. All the while his other end is being fucked wide open. No cock under ten inches. Every one passing the “RedBull” test.

He’s quickly reduced to something mindless and begging.

His fingers clench with the jackhammer thrusts into his ass, dying to grab and jerk other cocks his bonds won’t let him reach.

His torso is bathed slick with sweat while the chosen thirty use him. His tits and belly and cock get painted with the cum of his studs, but most of it goes into his sloppy, greedy holes.

 _And after the 3 hours are up?_  

The guys leave. Spent and happy. And John does a final video sweep with his hand-held of his gorgeous slut.

Derek's ass is bruised from spanking. His asshole gasps and gapes, dripping and raw. His flat stomach bulges from all the cum pumped into him. He lies there. His black mask webbed with drying white.

His panting mouth hangs open with cum still in it, waiting for the order. He's been holding it in his mouth for a while. John finally tells Derek to swallow.

 Then John sets down his camera. Fits a solid, fat plug in Derek's ass. Gently unties his shaky limbs. Kisses his forehead and helps him up off the table. Arms and legs so heavy, too exhausted to move.

 Lowers Derek to the floor so he can lick up all the cum that dripped onto the hardwood from his mouth and his ass.

 While Derek's doing that, John goes and runs a bath.

 Once Derek's done, he crawls to the bathroom and John eases him into a sunken tub. Slides in with Derk after and there under the bubbles pulls the plug and sticks his cock in Derek's well-used asshole.

Gently fucks Derek to sleep, that broad back against his hairy blond chest, while the afternoon’s unedited video footage plays on the big screen, mounted to the bathroom wall.

 

 

The End.


	2. Oct 2 - Ass Worship | Begging | Medical play | Watersports

Oct 2 - Ass Worship | Begging | Medical Play | Watersports

 

It’s spring training and Scott loves his job with the Beacon Hills Wolves' minor-league baseball team as Deaton's assistant medical/therapy tech.

He loves the sense of helpfulness he gets when he's easing all the teams’ various aches.

But that's not the only thing he loves.

He also secretly loves being around all those hard athletic male bodies. The daily show he gets working with the players, all those ripped muscled studs in their prime, their body hair, their stink of testosteroned sweat.

But what thrills him the most is the fact his job sometimes allows him to touch them.

Right now though, he's only allowed to watch. Not that he minds. Because at the moment his job calls for him to observe Derek Hale on the treadmill, Derek Hale, lead batter who’s wearing nylon shorts cut high enough that they barely cover the cheeks of his amazing ass.

Scott’s always been an ass man and he could easily stare at Derek's, in particular, for days.

So it’s a wonderful sort of torture, the scene before him. He’s tempted with Derek’s every footfall. With each impact, Hale’s round globes jiggle wonderfully. It's mesmerizing the way they bounce and flex. The way the thin nylon shifts with every stride.

Then, unexpectedly, Derek stumbles. He turns off the machine quickly and hops off the treadmill with a wince.

Turning around he sees Scott. Scott, who feels the heat rising to his face thinking that perhaps Derek caught him watching. But he's lucky because instead when Derek looks at him, his pained eyes suddenly light up.

“Hey Scotty Doc, I’m not sure what just happened.” The nickname the team has given him rolls easily off Derek’s tongue. “I think I might have pulled something in my glutes?”

Deaton is off right now doing physiotherapy out on the field with another player, so attending to Derek's new ailment falls entirely to Scott. And he’s praising the gods for this.

“Why don't we stop then and see what's going on? Let’s go to the office.”

Derek follows him easily into the back room. Limps after him, rubbing his left ass cheek, his green eyes wide. “Maybe I didn't warm up enough…”

Scott ushers Derek into the clubs’ small exam room/office and closes the door behind them.

"Show me just where it hurts now.”

Derek reasserts his grip on his left butt cheek. “Could be just a Charlie horse, maybe?”

“Or it could be that your muscles are over-tight,” Scott offers in reply. “Do you mind if I take a closer look?”

Derek laughs, “Isn't that what you're here for?”

Scott can't believe his luck when he gets to put his hand on Derek’s butt cheek and doesn't have it slapped away. He begins to caress that flesh, so supple under his hand, firm, yet soft at the same time.

“Maybe a simple massage would help?”

Derek’s dark brows furrow with his thoughtful frown but he nods. Scott wants the jock's eyes off him because he's getting hard already.

"Hop up on the table there.”

Derek complies without question, laying down on the vinyl-covered examination table, which is sort of a shame because being on his belly means Scott loses the visual of Derek’s massive bulge. But that’s okay because he’s really after a greater prize here.

He begins to rub his hands up the sides of Derek’s thick hairy thighs. His hands slip and slide against the slick fabric made hot by Derek’s body. When Derek’s posture belies no tension Scott takes a risk and tugs at his shorts’ hem.

“So, do you mind if we take these off?”

Derek’s dark head is cradled on his arms. His eyes are closed. When, after what seems like an eternity, he shrugs his broad shoulders and mumbles "go for it," Scott grabs the waistband of his shorts and slowly begins to lower them.

Now, he’s seen Derek in the showers before but this is his first time so close. It's just as amazing as he imagined.

His squat-built ass is framed by a baby-blue jock that looks so perfect against the dual tones of his tan line. The fleshy globes of his butt are round and supple. Skin flawless. Not a blotch or a pimple. Like a brunet peach, the fruit of Derek’s cheeks wears the perfect coating of soft dark fuzz.

Scott places both palms on Derek’s ass cheeks and begins to rub and fuck but his skin is hot and slick. Derek shifts a little in discomfort and moans softly when Scott finds all his tender spots. “Fuck that feels good,” he sighs.

And the med tech is damned if within less than two minutes Derek begins to push back into his hands. Scott's eyes grow wide when Derek’s hips take on a more aggressive pump and it quickly becomes clear his patient is frotting himself against the padded table.

“I don't know if what you did to yourself... If it's just muscular,” Scott says pushing his luck again. "Or if maybe it's more internal."

Derek turns his head back and looks at him with a question in his eyes. But seeing the lust on Scott's face he gets the picture quickly and a slight smirk quirks his lips.

“Do whatever you need to, Doc,” he says with a sly smile.

Permission granted, Scott’s breath catches in his throat. He grabs big handfuls of Derek's fat ass and pries his cheeks apart. The treasure he's been longing for and lusting after for the last 5 weeks finally revealed to him.

Derek's hole is dusky and sinfully shy looking, nestled within the nest of damp fur that rings it. As Scott marvels at it, he runs a finger down the crack of Derek's ass is rewarded with a delicious moan.

“Are you just going to tease me, doc?” Derek gruffs.

Scott doesn't need any more encouragement than that. He dips his face down into Derek's ass-crack. Slick with cooling sweat and so gloriously musky from Derek’s exertion Scott buries his nose into it and breathes deeply.

Like a connoisseur of rare liquors, he follows his sniff test then with his tongue for a taste.

The sounds Derek makes the moment Scott starts laving his asshole are just as delicious as his flavor. It’s an addictive combo and it renders Scott voracious. Soon his hands on each cheek are hard pressing those beautiful lobes apart so he can get in deeper to Derek’s rich, dark core.

Derek's hips rise off the table to grind back against his tongue. All Scott’s senses are filled: his eyes with the glory of Derek’s skin, his mouth its flavor, his nose the scent of ass and man and sweat, his ears with the sounds of Derek's pleasure.

Caught up in this sensual fervor Scott could worship this ass for hours. But then he hears the hitch of heavy breath and grumbly kind of whine.

“I need more, Doc,” Derek gasps out. “Come on. Scotty fill me!”

Scott tears himself away from Derek's hole to bite one of his plump cheeks. It’s a silent “I’ll fuck you when I'm good and ready” response to the athlete’s pleadings.

Fuck, but the texture of Derek’s meaty ass between his teeth is rich as butter. So glorious in his mouth. Scott is glad the door to the office is closed because despite his nipped admonitions Derek’s whines and complaints just grow louder and rougher.

“Fuck, I’m aching here. I need you in my ass now, Doc.

"Raw.

"Hard and heavy.

"Pleeeze, godammit, Scotty breed me!"

By now Derek’s moved so he’s kneeling on the table, ass up, ready and presenting. His thick cock and heavy balls remain caught and straining in his jock, but even so, Scott can smell the wet musk of Derek's arousal ad knows that pouch is soaked.

But he ignores Derek’s pleas. Doesn't stop licking. Just shifts things so he makes room for his fingers to join his tongue.

Worked over so thoroughly already, Derek's asshole is wet and soft and opens up easily for his fingers. And fuck it's wonderful the way Derek uses his ass, grinding back like a true whore, riding his digits.

Derek is grunting loudly now, his luscious mouth fallen open. Ragged pants sound with every breath. He starts begging in earnest.

“Fuck, Doc! I need your cock in my ass now. Please... Fill me up!” Come on, I can't wait anymore!

"Please... Fuck... I need it so bad... Please... Fuck this bitch!"

Grabbing a little salve-filled bottle from a nearby medical tray, within moments Scott's thick, hard cock is freed, slicked, and ready. He reaches for Derek’s hairy calves and grabs them, jerking that perfect body half-off the table. Bending him over it, so his hole at the perfect height for fucking.

He slides into Derek's ass with a glorious ease. But once his cock is ensconced between those luscious ass cheeks Scott can't hold back.

He’s needed to own this for far too long to have any restraint.

He bucks into Derek hard and immediately pounds. Derek cries under the fury but submits. And once Scott wears himself out enough to slow, Derek immediately picks up the slack, bouncing his fat, slutty bottom on those nine inches like a seasoned bitch.

When Scott can't take it anymore, the buzz in his body coiled tight and ready to lash out its climax, he grabs Derek’s hips hard enough to bruise and unleashes one final frenzy, until his balls hitch and he dumps his load deep into Derek’s perfect ass.

He’s surprised when he begins to pull out after he finishes, the way that Derek obviously skilled muscles clench greedily around him trying to hold him.

“Can't leave yet,” Derek whines. “Come on Scotty. I need more!”

Scott's balls are drained but it's clear that his this jock-bitch is still hungry. He's not sure what to do. But then he gets an idea.

“How about a little internal heat therapy, Derek?”

The glance Derek casts back at him over his shoulder is puzzled but confusion quickly turns to ecstasy when Scott opens his bladder begins to piss, flooding Derek's needy hole.

“Hell yes, Doc. That's good…. Fuck…  That's what I need! Fill me! Fill my ass up!" Derek moans as his guts are flushed with a long, strong jet of hot urine.

When Scott's done pissing he pulls out. There’s no begging this time: Derek is content.

“Crawl back up on your knees on that table. Grab those slutty cheeks and show me…”  

The order is obeyed.

As Scott stuffs his cock back away he admires his handiwork. Amber fluid mixed with creamy white drips down Derek's taint. Derek’s hole is puffed and fuck-bright. And Scott swears that six-packed belly actually looks a little distended.

 It fills him with pride, the idea at this athletic stud is swollen with his fluids.

He steps away, leaving Derek on the examination table presenting like the bitch he is: head down, hands still spreading his flushed cheeks, his hairy ass still high.

“I want you to hold that there and keep it in for the next 20 minutes,” Scott says. “Doctor's orders.”

Then he moves over to the office’s desk and settles in his chair in the perfect position to keep an eye on Derek’s ass. This way, he can make sure the ball player minds while he writes up Derek’s progress and jots down future 'therapeutic' recommendations for Deaton.

 THE END

**Notes for the Chapter:**

> Derek's costume - slutty athlete
> 
> Scott's costume - team medical assistant
> 
> *gives them treats*
> 
> Thanks for dropping by boys!
> 
> You too, readers.


	3. Oct 5 - Feet | Sadism/Masochism | Feederism | Shotgunning

Oct 5 - Feet | Sadism/Masochism | Feederism | Shotgunning

“Hey babe, I’m home!”

Derek glances up from the kitchen table where he's doing translations, his expression puzzled.

“I thought you weren't going to be home until dinner time.”

Stiles rattles heavy paper bag he's holding almost translucent with grease.

“I had a little bit of extra time so I thought I'd bring you lunch.”

There's a look on Derek's face that's slightly uncomfortable and Stiles would be lying if said it didn’t give a little kick to his dick.

“Stiles, I haven't even had a chance to recover from that breakfast you fed me. I'm not even really that hungry.” Derek shifts in the new chair they recently bought for him.

Stiles sets the bag down on the table and pulls out a paper-wrapped burger, knowing full well the effect this will have on his lover.

“That’s too bad because I got your favorite.”

He walks closer watching Derek's nostrils flare at the scent, knowing he's going to win this battle already. Derek pushes back from the table and Stiles takes this opportunity to slip between his legs and sit down, perching his skinny ass on one of Derek's increasingly thick thighs.

He unwraps the burger and wafts it under Derek’s nose. "Come on, sour-wolf, just take one bite for me. You know how good it makes me feel to feed you.”

Forty-five minutes and four hand-fed burgers later Stiles jerks off while still in Derek’s lap, his dick hard and the fingers on his cock oil-slick from the burgers. After he comes, he hand-feeds this to Derek too. Patting his sweetheart’s distended belly while Derek groans in his fullness.

Slipping off Derek’s lap then, Stiles kneels between solid thighs. With Derek raising his hips to help, he pulls down the loose sweats hiding his boyfriend’s massive dick so he can help himself to his own ‘liquid lunch.’

Of course, Stiles isn’t greedy, so he shares this with Derek also, once he’s gotten his mouth full.

The taste of Derek's come is slightly rancid because of all the junk food he feeds him. Not that Stiles minds this terribly, he's found the flavor of conquest is often bittersweet.

After making sure Derek has swallowed, Stiles kisses his boyfriend goodbye, sucking the grease from his lips before he heads back to the station.

* * *

“Come on, Derek! Let me see!”

Stiles sits on their king-sized bed staring at the bathroom door.

“I don't know… I’m not really comfortable in this,” Derek calls from behind it, his voice filled with uncertainty.

“Well, bring that sweet ass out here and let me be the judge. How about that?”

Derek emerges shyly from the bathroom a minute later wearing Stiles’s most recent gift. The cheeks of his scruffy face are hot with blush, but those aren't the cheeks Stiles sees: his eyes are too focused on Derek's ass.

It’s a sweet ass indeed, made even sweeter by the spell he’s has cast on it so that whatever he feeds Derek, no matter how much his man exercises, all the fat goes straight to those glorious globes.

Since they've been together, Derrick's ass has increased so that it's now at least four times the size it was before. It's gotten to the point where he has pretty much made himself housebound: unable to find any sort of pants that fit him well and too self-conscious to leave the loft.

Which is semi-disappointing, because as much as Stiles loves being able to have Derek all to himself, he loves, even more, the stares and whispers they get when he takes him out in public. Everyone awestruck and jealous of the gorgeous bottom (in more ways than one) that belongs to him.

Stiles knows it’s slightly sadistic, the glorious twist in his gut and the iron he gets in his cock at what he's doing, well aware of what the cost is for Derek in terms of his confidence. But he simply can't help himself. His eyes fix on the most fantastic bubble-butt in God's creation right now and he believes it’s all totally worth it.

Fuck, he loves Derek’s waxed ass so much, all round and firm and flawless. One of the greatest things about Derek's werewolf biology too is no matter how fat his boyfriend’s ass gets, it will never be marred with a single stretch mark.

“Goddamn, you look amazing, babe! Come here and let me see you closer.”

Derek shuffles over. The weight of his posterior makes him slightly unbalanced and so he moves a little slower. (All that much easier to catch.)

“I just don't think it's me…” Derek says. His hands come dangerously close to trying to obscure his jiggling cheeks. Stiles quickly slaps them away, breathless and ready to worship.

“No, hot-pink is definitely your color.”

Stiles runs his hand comfortingly over the massive bulge at Derek’s front, barely contained by the thong’s pouch. But then he leaves off Derek's cock, which grows immediately hard at his touch (another wonderful side effect from the spell and one that further binds Derek to him).

“Turn around for me,” Stiles gently orders. His breath catches at the way the thin, hot-pink thong string in the back is completely swallowed up by the massive mounds of Derek's smooth ass. Putting his palms reverently on them, his hands look so small against their glorious expanse.

Delighted, he bobbles his hands making the fat cheeks bounce deliciously.

The only thing that would make this picture complete would be if Derek would finally agree to get a tramp stamp of his name just above this glorious booty. Stiles still doesn’t really get what Derek’s issue is about the tattoo. After all, his love is going to be just as permanent.

He hasn’t pushed for the ink too much lately though. In this instance, he can be a little patient. Stiles knows it really just a matter of time before Derek caves (just like everything else he’s suggested).

“Fuck, I love your ass, Der.” He leans forward and kisses each cheek tenderly.

His lover is not as convinced.

“I don't know Stiles. I think it's gotten even bigger today than it was yesterday. Maybe we should see a doctor or talk to Deaton again?”

It's the perfect excuse for Stiles to whip out his trusty measuring tape. “Let me check, babe.”

Unbeknownst to Derek he's been meticulously documenting their progress and posting this on the ‘feeder’ site he belongs to, along with all the photos and surreptitious videos he takes. His sweet boyfriend has no idea just how ‘big’ a hit he is or how fast his internet star is rising.

Straining around Derek's cheeks, the tape doesn't lie. His ass has grown another half inch since yesterday. Stiles, however, has no problem telling a fib or two with Derek’s hearing of him spell-blocked so everything rings true.

He grins as he rolls the tailor's tape up and sticks it back in his pocket. “Your just imagining things, Der,” he says with a grin. “Now, how about you try on that lime green mesh number I got you. Bet it’ll look gorgeous with your eyes.”

* * *

 

“That feel good Der?” Stiles asks as he rubs.

Next to Derek's ass and his fat, leaky, foot-long cock, one of the other things Stiles loves most is his lover's feet. And why shouldn't he? They're perfect. Not a corn or a callus, the nails perfectly shaped and pedicured (the results of his handiwork, Stiles is pleased to say), every toe straight and shapely.

Derek answers with a groan. “I don't know why they’ve been aching so much,” he grumbles into a pillow as he lies face down on their bed.

“I think you just need to take it a little bit easier, babe.”

Stiles rises from the mattress in order to push the open box of chocolates he brought home, one of five, up the covers toward Derek’s head. Then he reaches for the bottle of massage oil on his desk, stopping along the way to adjust the position of his laptop to make sure the cam is getting a perfect shot of Derek's feet.

“I feel like I'm hardly on them at all anymore as it is, Stiles…” Derek mumbles around a chocolate.

When he threatens to roll over so he can look back as they talk, Stiles delivers a sharp smack to his ass that makes those panty-straining cheeks jiggle.

Derek grunts but stills and Stiles has no doubt his lovely pain-whore has a hardon now, trapped between his still-flat belly and the mattress. He smacks Derek’s fat butt again for good measure.

For those he’s currently filming for, who subscribe to his other fetish site, these love taps will be an extra bonus. But while he’d be more than happy to spank his lover’s bubbled posterior purple, that’s not the point of this particular session.

So, instead, he lovingly oils Derek’s feet now, his fingers slipping gracefully over their smooth surface. He dips between each wonderfully articulated toe, careful not to tickle (too much, anyway). He frowns a little bit, however, because the weight of Derek's ass is now causing his feet to swell. Hopefully, this won’t be too apparent in the video.

“Got everything you need, sweetheart?”

Hearing the confection-muffled “yes” from the head of the bed, Stiles quickly pushes his jeans down and grabs his hard eight-inch cock.

Despite the slight puff of Derek's oil-glossed feet, he’s able to slip on a couple toe rings without much problem. He adds a leather anklet for good measure. Because who doesn't like a little bling? Then he dips down to press the kiss to the bottom of each foot, adding a little nip directly to the left one just so he can watch those wonderful toes curl.

Moments later, while Derek is grazing contentedly on chocolates Stiles rubs his cockhead over the balls of Derek's feet before finally grabbing his pliant lover's ankles and pressing Derek's feet together to make the perfect cock sheath.

After a good 15 minutes of frotting fuck, Stiles’s beautiful big-bottomed fuckpig’s little piggies are all dripping in a fresh coat of come.

* * *

“I promise you, Der. You’re gonna absolutely love this!” Stiles adjusts the camera on its tripod, so pleased he doesn’t have to hide his filming anymore. His subscription rates have tripled now that they’ve gone high def.

“I… I’m still nervous…” Derek says softly. He's looking over his shoulder trying to get a glimpse of Stiles but it's impossible around the hugeness of his ass.

“I know, babe,” Stiles soothes. He understands Derek's hesitation, his lover has been through quite a lot in the process of his perfection He doesn't stop his preparations but he does tickle his fingers reassuringly across the ink that now brands Derek as his.

Fuck but he loves seeing his name just above that ass on their videos.

“Just trust me. I've got you.”

Stiles comes around to the head of the bed and kisses Derek’s toffee-sticky mouth. He licks his lover's lips before popping the ball gag in and buckles it snuggly at the back of Derek’s dark head.

Derek isn't otherwise bound, not really, but he is suspended slightly up off the bed by the sling Stiles had installed. Wrapped under his belly it helps, given the weight of his prosperous backside, to keep that gorgeous ass lifted high while he’s being fucked and hold it in the perfect position for the camera.

“I'm so happy you're finally letting me do this. And all your fans are going to be too!”

Gagged Derek doesn't answer but as Stiles walks back around behind him again, he sees the wonderful burning blush dripping down bare shoulders. He turns the camera on, claps his hands, and says “Showtime!” And this is how it starts.

It begins with the slow removal of the bright-red panties that cling, delightfully tiny, stretched to capacity over the gorgeous mounds of Derek's butt.

Style slips these off and set them to the side. They'll be sold after he releases the video. (The auction prices for Derek's used drawers is really quite remarkable.)

Then there’s the massage with oil to make Derek's fat cheeks shine.

It's been over a month now since he's been able to properly fuck Derek’s hole. His lover's ass has gotten so big it's almost impossible to access it. Not that Stiles minds. There are few things he likes more than frotting his dick, watching it caught between the pressed cheeks of Derek's wonderous flesh bubbles.

Besides, that's also what Derek's mouth is for.

Pressing his lover’s glorious globes apart now, Stiles reveals to the camera the plug that he has carefully worked in. He filmed all their preparation earlier. Truth be told, it all but killed him having to give Derek his enema. The bonus is, however, that once they're done here, he gets the opportunity to fill Derek back up again.

Now though, there are other ways he plans to fill his dear boyfriend. After fucking the plug in and out to work it loose, Stiles greases up his hand with Crisco.

Derek takes his first fisting like the beautiful submissive slut he’s become. His own fists grip into the in the sheets as he fights the pain but he takes it.

Even with the gag he makes the most wonderful sounds and Stiles can't wait until later when he'll have a chance to watch the feed from the camera pointing at Derek's face.

It takes some work for him to get inside to get inside Derek's asshole. That's okay though: like was said before, he’s patient. After all, he’s spent months slowly penetrating Derek in so many other ways.

When he finally does get just his hand inside Derek’s juicy man-cunt, the round globes of Derek's ass pooch out so far they greet his elbow.

The way Derek's bubble butt jiggles as Stiles opens his lover up and begins to pump is nothing short of pure poetry. Derek writhes and moans as his arm reaches up so high so deep Stiles imagines he can almost touch Derek's heart.

“God, look at you, my sweet fuckpig. You love this, don't you? Listen to you squeal in pleasure. So beautiful, babe. I'm the luckiest guy in the world!”

Ignoring the sounds of Derek's harsh sobbing, Stiles begins to use his free hand to spank Derek’s bountiful butt. Each hard smack paints it a deeper shade of red until his boyfriend's ass is hot and glowing.

“God damn!” Stiles growls, “you are fucking perfect! I know you love it, Der. I know you need it too!”

The truth of his statements is confirmed when he reaches under (because he can't reach around that massive ass) and grabs ahold of Derek's 12-inch prick. It's rock hard and profusely leaking.

It takes a little coordination but soon he has one fist pumping deep in Derek's ass, the other shot-gunning his needy dick.

The cry Derek makes when he comes is louder than any other so far. His fat cock shoots its heavy load and continues to twitch in Stiles’s hand for two full minutes after. When Stiles finally pulls his hand out, Derek collapses on the bed suspended only by the sling under his belly.

Stiles continues to film Derek through the cleanup while his lover lays there wrung out, exhausted.

After his bubble-butted beauty is all wiped down, he undoes the buckle at the back of Derek's head. He runs his hand through sweat-soaked hair. Twisting his fingers in wet bangs Stiles uses this to lift Derek's face to meet his. He drinks in the dazed green eyes and kisses the drool on the corners of his darling's mouth.

“Hey, Der, what do you say I call an order in? I kind of feel like pizza.”

 

**Notes for the Chapter:**

> Derek's costume - Big bottomed- bottom
> 
> Stiles costume - deputy pervert
> 
>  
> 
> Thanks for reading! I'd offer you a treat but Stiles fed them all to Derek this chapter.


	4. Oct 12: Licking | Pet Play | Rimming/Analingus | Costume

**Summary for the Chapter:**

> October may be over but Kink-tober lives on...
> 
> Today - Licking | Pet Play | Rimming/Analingus | Costume.

**Notes for the Chapter:**

> What, ABD? An AU dystopia where everyone fucks Derek? How rare for you...-snickers-
> 
> Welp, this particular rut of mine is like the crack of Derek's ass: it's deep and I love it.
> 
> So here's pony play Derek for your enjoyment.
> 
> As a head's up, there's major non-con, mind control, and all manner of other dark things in this chapter, so if you're squeamish... You know the drill.

Oct 12: Licking | Pet Play | Rimming/Analingus | Costume

 

Today some of the Alpha pack gathered around Derek to measure his progress. He stood perfectly still while the twins harnessed him up but his broad chest and ridged belly heaved with anxious breaths as they fastened him into his black leather tack.

As soon as their new Hale pony had arrived at Alpha Pack ranch two months ago, everyone had been eager to ride him. But Deucalion forbade it until he was sure Derek had settled in.

When they’d first unloaded him from the trailer with the others, their newest steed looked rough from the roundup and his long travels. Despite his disheveled appearance though, he’d fought them like hell. Given his strength and quickly understanding his stubbornness, Deucalion immediately remanded him into the care of the twins.

Since then, Ethan and Aiden had been working hard with Derek every day. It had taken them weeks, he hadn’t been easy to tame, but after a lot of extensive ‘hands-on’ training, finally, he was coming along well enough for his first open road excursion.

Derek’s sleek, oiled skin glistened under the sun. It had been no small feat to strip his body bare of all its original fur, but his newly-hairless hide glowed, pasture-tanned, unblemished by anything but a few lingering crop marks, and it showed off his rune-inscribed harness beautifully.

With each touch of the twins, Derek’s thighs, heavily thickened from all his training workouts, flexed as though he wanted to flee from the paces he knew he’d soon be put through. Once he was well-secured, Deucalion stepped up to him.

Humming in approval, the Alpha pack’s leader placed a hand on one of the pony’s plump ass cheeks and jiggled it, testing its heft. In addition to his legs, Derek’s equine training had made his supple butt rounder and wonderfully firm. Deucalion traced a finger over the brand on his left ass cheek. Even though it was no longer red and blistered, the Hale pony still shied at the touch and it took the twins a minute to get him settled back down.

Of course, once they had his bridle on he was much easier to handle. And while perhaps the blinders on the sides of its headstall did hide his wild green eyes a bit, Derek otherwise looked truly gorgeous in this tack. What, with the jaunty leather ears that perked up from the bridle’s back, as well as the fake mane that draped down to just the top of his broad, bare shoulders.

But the way he struggled when they pried his mouth open to fit him with the stubby, hollowed penis-gag-bit, made it clear there was still some work that needed to be done. It was the same when even bitted, booted, and harnessed, Derek continued to fight Ethan while his trainer forced him to bend over.

“This’ll be his first time taking the tail, boss,” Ethan warned.

“Better get to it then. I plan to mount this steed today.” Deucalion’s eyes roved, hot, over Derek’s well-muscled flesh. “He’s gonna need the stretch.”

With a nod Ethan held Derek’s buttcheeks apart while Aiden worked the tail plug into his still virgin-tight pony ass. Derek stamped a booted foot in protest of the greased rubber cone being worked into him but Aiden was patient and more than happy to plug-fuck the resistance out of the stubborn stallion.

It took some work, the way Derek shifted and bucked, but by the time Aiden finished, Derek was finally being a good boy again. He remained still, bent over, taking the plug popping in and out of his asshole silently. In fact, his mouth worrying the rubber dick it was gagged with and the long string of glistening pre-cum dangling from his bouncing hard dick were the only signs left of how this plug-stuffing affected him.

At last, Aiden stepped away. There was a murmur of appreciation from the Alphas gathered around as they admired the plug’s long, glossy black tail hanging down from between Derek’s round ass cheeks. Now subdued, Ethan led him over to Deucalion’s cart. Ennis stood next to it, the reins of his own pony, Boyd, held loose in his hands.

Ennis moved around, climbing up into his cart. Deucalion hopped up into his buggy as well while the twins buckled Derek in. The new pony was too busy trying to get a good look at Boyd to put up a fuss.

“I think it's time we take this stud out for a test drive. He seems awfully lively still. Probably wouldn't hurt to run him out a bit.”

The twins stepped aside and Deucalion punctuated his words with a crack of leather reins against Derek’s ass. The Hale pony stepped out immediately, well trained enough to know the whip quickly followed unheeded commands.

The road leading away from the stables was wide enough Ennis was able to bring his cart alongside. With another shared sharp crack of the reins soon both Alphas had their ponies set out at a crisp trotting pace.

“I heard they’re having to go farther and farther out to gather up new stock,” Ennis offered as the ponies trod along in the stylized gait they had to maintain to accommodate the hoof-boots they wore.

“Yes. The wranglers said they had to go clear to California for this round up again. Even then, there weren’t many. Lucky for us that new pack your Boyd came from hadn’t already been poached clean by others.

“That wrangler, Kraven, said the Stilinski kid’s blog, the one that led them to Boyd, was still active. Even more so after he caught your pony there.”

Derek gave a loud huff at a fresh slap of the reins against his bare ass. Deucalion grinned. "Thank the gods for teens and their internet stupidity...

“Still, what a haul, huh. Three new stallions and a mare from that loose pack. And I’ll tell you again, we were lucky to get Derek, the bidding for him was particularly fierce. Every pony-loving pack ranch wants wild caught, it seems. But true-blooded and not turned… That’s something rare.”

Ennis gave a gentle tap to his own steed making sure Boyd kept pace. “I can see why he was so spendy: were-born, wild, with such good confirmation... And as for wild caught, can you blame those other ranchers? Or any of us, really, for the preference?

"Half the fun of training a pony up is in the challenge of breaking them.” Ennis nodded to Boyd as if to illustrate his point, his project of six-months, so well trained now he’d already anticipated the coming command and sped up.

Deucalion grunted in agreement and turned his eyes back on his own pony. Despite Derek clearly being unused to the plug, the way his long black tail swished back and forth as he moved was marvelous.

Much work had been invested in the trails surrounding the Alpha Pack's ranch to ensure they were easy for their ponies to manage in their specialized boots. Further out on the road now the creaks of the wheels and the soft shifting of leather filled all the spaces between Deucalion and Ennis's continued spates of conversation.

They hadn’t gone too much farther, however, when Derek started to act up. A master handler, Deucalion quickly remedied this with a number of short sharp lashes of his bane-soaked whip across tender cheeks, spurring Derek into a run.

While his own solid, dark steed needed no cropping, Ennis kicked Boyd’s pace up to match. Before long, Derek's hide glistened with sweat and he panted heavily, his breath whistling through the gag-bit in his mouth.

Deucalion had no mercy though. Knowing the only way to ensure an obedient steed was to fully impress upon the Hale pony who was boss here, he and Ennis ran Derek and Boyd for miles until Derek was all but stumbling, barely able to pick up his heavy-shod feet.

Seeing a familiar grove of trees up ahead, a small creek running through it, Deucalion motioned to the other Alpha to follow. They pulled up and parked in the shade to give their weary pacers a breather.

* * *

It wasn't by chance he picked this place to stop: it was a well-known spot, usually used in more advanced stages of training. Jumping down from his cart, he unhitched Derek quickly. Before his run out pony knew what was happening, he had been led over to a smooth round boulder with several iron rings embedded in its surface.

Derek’s reins were quickly tied off. His hands, which had previously been hitched to the rails of the cart, were clipped, one each to the leather bands encircling his thighs. His legs trembled with fatigue as they were roughly kicked apart and the steel rings sewn fast into the thick leather of his boots were clipped to other rings, spread wide at the boulder’s base.

Bridle hitched before him, forcing him to bend over the rock, ankles hobbled below him, there was nowhere for Derek to go. Even so, he began to buck and twist, fighting against this bonds.

“Lots of fight, this one,” Ennis said, leading his own unhitched pony up to the stone. Seeing the way Boyd eyed Derek, he unhooked Boyd’s bit from the bridle and pulled it from his mouth. “Wanna say hello, fella?”

“Good idea.” Deucalion voiced his approval. “I know the twins have kept Derek isolated so far in his training.”

Derek stilled when Boyd’s shadow fell upon him. Drool dangling from the black steed’s chin dripped on his shoulder making him shiver. His tremor increased as Boyd leaned over and licked his own spit back up from sweat-slick skin.

“He should start getting used to the herd. And I know Boyd here will give him a first-rate introduction.”

The Alphas chuckled, watching as Boyd continued to lick, the salt of Derek’s sweat clearly an agreeable flavor. Soon in addition to his industrious tongue, Boyd was placing sucking kisses and nips rough enough to bruise across Derek’s shoulders and neck.

While Boyd distracted, Deucalion grabbed Derek’s cock. Long and thick enough to be a true pony’s dick, Derek’s massive rod was still erect from the rub of the plug and angry-looking from its thrashing against his thighs as he’d run. The Alpha clipped a chain to the heavy ring that ran through Derek’s now foreskinless cockhead.

“Like how pretty his cock looks now, ringed and all bare for us.” He rubbed his thumb over its glossy, pierced tip.

Derek’s altered vocal cords loosed a strangled whinny when Deucalion released his cock and it was roughly jerked downwards by the chain the Alpha had also dropped.

“Hush” Deucalion chided. “You should be thanking me, not making a fuss. That lead will keep you from getting abraded unless you like the idea of frotting a rock.”

The chain rattled lightly as it swung between quaking thighs, the stainless steel ball weighting its end bobbing merrily. The tip of Derek’s dripping dick bobbled too. True to Deucalion’s word when the weight settled, at last, it kept Derek’s dick pulled down. There was just enough room between his body and the boulder that if he leaned back against his bonds his shaft wouldn’t rub against stone.

“You going to take him for his first spin?” Ennis asked, watching Deucalion smooth a large hand over Derek’s ass and toy with the plug. The older Alpha nodded and smacked Derek’s flank hard when the pony thrashed at his touch.

“You know how much I love being the first one up on a pony’s back.” They laughed at the double meaning while Deucalion worked the plug loose despite his steed’s protests.

“Why don’t you lead Boyd back over here. He’s had some salt, but I bet he’d like something sweet too…”

It took a few minutes of hard spanking for Derek to still enough for Ennis to get his pony situated. Once Derek went lax though, a moment later Boyd was on his knees industriously licking between hot, spank-red asscheeks. His eager mouth suckled at Derek’s puffy rim, his broad pink tongue slipping easily into the bound pony’s sweet-greased gape.

“That’s right, get that virgin hole ready,” Ennis grinned on in approval while his pony worked like he’d been trained to between the plump globes spread wide by Deucalion’s hands.

Derek continued to remain pliant, for now. Forehead pressed to the rock he groaned loudly at the sensation of his ass being so skillfully eaten out. His noises didn’t stop either when Ennis finally pulled Boyd away so that Deucalion could slip around and slide his fat Alpha cock into the hole Boyd’s tongue had just vacated.

Once Derek realized what was happening though, he panicked again. By the time Deucalion got him re-settled this time, Derek sobbed into the stone and the color of his ass cheeks had turned from deep red to almost purple.

“Fuck, that feels good, “ Deucalion sighed as the head of his cock finally popped into Derek’s hole. He took a moment to savor the tight hot sheath of Derek’s channel around his cock. The Alpha grabbed the harness straps at Derek’s shoulders and the Hale pony tensed and whimpered as Deucalion used these to pull his tender ass deeper onto his invading prick.

Ennis walked Boyd around to the other side of the rock and loosely tied off his reins. Boyd immediately widened his stance and leaned forward. Fat ass out and back beautifully arched for reception, the position put him almost head to head with Derek.

“Nice day for a ride,” Ennis sighed, popping out Boyd’s plug and plunging his dick into his pony’s well-trained hole. Unlike Derek, Boyd was eager for his fuck and worked his bubbled butt back, grinding down on the Alpha’s dick.

“Mmmmm...”Deucalion answered back lazily rocking his hips. He had his hands full now of Derek’s whip-stained bottom, the pony’s bruised cheeks pried open as he watched his thick alpha dick lazily fuck the no longer cock-cherry hole.

“Do you mind?” Ennis motioned to Derek and the older alpha gave a nod of assent. With that, he leaned over Boyd’s broad shoulders and unclipped Derek’s bit, pulling the stubby penis gag from between Derek’s lips.

The Hale pony’s tear-filled green eyes flashed gratitude, then surprise, as his empty mouth was almost instantly filled with Boyd’s tongue. When he tried to shy away, the other pony’s ardent mouth pursued him from across the rock.

Deucalion grabbed the back of Derek’s bridle, holding his head in place so Boyd could more easily catch him.

“Probably just not used to the taste of his own pussy.”

In response to Ennis’s comment the older Alpha snorted and snapped his hips hard enough to make Derek gasp, though the sounds were once more muffled by Boyd’s dominating tongue.

“Well, it’s a flavor he better learn to love,” Deucalion growled and only slowed his pace when Derek finally submitted and began kissing back, tentatively at first, and then suddenly fierce in challenge to the other stallion.

Watching this display Ennis grunted, “they look pretty together.” He kicked his fucking pace up then from a walk to a fast trot.  

“They do,” Deucalion agreed, speeding up the pulse of his hips to match. The two ponies continued to kiss until the thrusts of their riders got too jarring.

“Fuck, this ass is so tight…” Deucalion groaned as his hips ramped up to a gallop: Derek’s cunt was too fresh, too hot, too slick, too good for him to last. He rode the virginal hole hard to his climax, grunting loudly as he pumped a heavy load into sweet new-pony pussy.

Once his cock stopped twitching Deucalion stepped away, leaving Derek lying limp and heavy against the rock. He stood for a minute, watching the wrung out pony pant while Ennis continued to ride his own steed.

Ennis ribbed the older Alpha as he fucked, “Don’t you know there are some races where finishing first doesn't mean that you won?!”

Deucalion scowled at this but then his expression lightened. “You’d finish fast too if you been riding Derek.” He cocked a brow and offered, “why don't you try him now that I have him all loosened up for you?”

Ennis looked thoughtful but only for a second before he broke into a grin. “You know, they say you shouldn't switch horses midstream, but in this case, I think I'll make an exception.” With this, he slid out of Boyd and walked around to the other side of the rock where Derek’s ass lay open and waiting.

While Deucalion had a fat, solid Alpha shaft, Ennis’s dick matched his stature: it was a monster, as long and broad as he.

“Nice work,” he commented, admiring Derek’s still gasping cunt and the streams of Alpha seed dripping down his taint.

As Ennis fit his fat cockhead against Derek's purpled pucker, Deucalion stepped up and refit the gag-bit between Derek's gasping lips. It was a good thing too because even a stretched out as he was, when the Hale pony was finally breached, the sound he made wasn't a whinny but a bray.

“Fuuuuck! You're right,” Ennis howled himself as he pushed his way into the velvet heat of Derek's ass, wonderfully slicked from Boyd’s tongue and the older Alpha’s semen. Derek bucked against this fresh assault, but all that did was encourage his new rider.

“Yeehaw! Let em buck!” Ennis fucked hard into Derek’s writhing body and quickly ratcheted his thrusts up into a punishing pace.

Deucalion stood at the side and admired the Hale pony’s ass being pounded. The jiggle of fat ass cheeks and the drool of Derek's tied down dick was poetic. Then he stepped far enough around so he could see past Derek’s blinders.

Riderless, Boyd had returned his attention to Derek and, despite the jerks of the news pony’s head as he was fucked, was working diligently to lap up each salty tear from stubbled cheeks. Deucalion watched Derek’s weeping eyes suddenly pop wide open and his long lashes flutter.

“Kick it up a little faster!” he called out to Ennis.

The younger Alpha obeyed and within a few moments Derek's green eyes rolled back hard into his head. Between his thighs, the weight on his cock began to dance, now not from alpha pounding but from the twitching of his climaxing dick. Between his booted feet the ground below was suddenly painted with his seed.

“Good work!”

Deucalion’s praise was lost on Ennis, however. The way Derek's cunt clenched around the Alpha as he climaxed sent him tumbling into his own. Much louder than Deucalion, Ennis all but roared as he added his own load deep into Derek's ass.

“Fuck, that's a good ride!” he cried, delivering several sharp smacks to Derek's whip-welted ass.

He stood there a minute, catching his breath before he pulled out. When he stepped away Deucalion was there beside him to comment on the increased gape of their new pony’s well-ridden pucker.

“Looks like you put some real miles towards breaking him in,” the older Alpha chuckled.

Ennis ran his finger around Derek's puffed rim and dipped three into his cum-filled ass. “Look at that hole... I bet he’s stretched enough he could almost take Boyd.”

“Want to try it?” Deucalion arched an eyebrow and glanced over at Ennis’s pony. “After all you didn't finish your fuck with him and he's been so good with Derek I think he deserves a treat.”

Hearing this, Derek seemed to revive and the exhausted mount began to wiggle and buck. No doubt, on their run he’d been more than aware of the fat “horse cock” that dangled low between Boyd's muscular thighs.

“Looks like he likes the idea,” Ennis laughed, knowing that it was, in fact, the opposite.

“Well if you didn't break him in, this will for sure,” Deucalion smirked. “And it looks like Derek’s not the only one who’s excited.” There was no mistaking the gleam in Boyd's eyes as Ennis unhitched him and walked him around behind the struggling steed.

Deucalion pulled out his phone and flicked it to video. “Should’ve of thought of this earlier, but I know the rest of the pack will want to see this…”

Once Boyd was behind Derek, Ennis grabbed the stallion’s cock. It was long and almost as thick as a woman's forearm. Ennis pressed it to Derek’s cum-frothed hole. Both Alphas leaned in to admire the stretch as their new pony’s ass struggled to swallow the fat mushrooms head of Boyd's cut dick.

Derek screamed around the gag when the other stud’s cock pierced him and for good reason. The second Boyd felt his cock dip into Derek's wet-heat, he reared up and drove his massive rod in. Wasting no time, he began to buck, just as fierce and as jagged as any four-legged stallion might.

His own arms hindered, Boyd leaned over pressing his muscled body against Derek’s back for leverage. His breath came in loud snorted puffs as he tried to force the full length of his dick in. He hesitated briefly seeming to meet some internal resistance. Derek shrieked around his bit, his whole body trembling.

“Looks like he just hit the curve.”

Deucalion nodded in agreement with Ennis’s assessment. “And it looks like our new pony just passed out.”

Boyd didn’t seem to mind that the other stud had suddenly gone completely still beneath him and continued to feed his massive cock into Derek’s faint-lax bowels until he was at last fully accommodated. Balls deep, he began to thrust in a strong but much more measured pace.

Without all Derek’s protesting noises the grove’s pastoral soundtrack resumed: the burble of the creek, the shifts of the breeze, Boyd’s low huffed breath and the slap of his heavy ballsac against Derek’s taint.

“Look at him go, he’s really enjoying himself. Not often he finds a cunt that can take his whole dick.” Ennis’s gaze was glued to the flex of Boyd’s fine ass as he fucked. “Maybe you should consider gelding Derek, give Boyd a permanent pasture bitch.”

A slight shiver passed through the older Alpha’s shoulders at this suggestion. He looked away from filming to regard Ennis seriously. “You know outside taking their foreskins I’m never much one for cutting a stud. No, they can duke it out in the pasture later, though it might not be as much of a fight as you think.”

He nodded to the fucking ponies and turned back to his phone. Derek had roused it appeared, but rather than resume his struggles, instead, he was visibly pushing back onto Boyd’s thick dick, moaning softly. The coupling ponies made a pretty picture, fucking together, Boyd’s sleek dark muscles in contrast with Derek’s paler flesh, each one’s skin tones accenting the beauty of the others.

Unlike Boyd’s powerful composure, however, Derek was a mess. The gray stone under his cheek was stained dark with tears, snot, and drool and between his feet, the red earth was spattered. Derek shuddered and sighed as his own massive membered twitched and spit, adding to the muddied earth with another strong orgasm.

When this subsided, spent and oversensitive, Derek tried to squirm off the other stallion’s persistent cock. Boyd wasn’t having any of this though, he threw his full weight against the pony beneath him. Pinning Derek to the boulder he fucked him through two more orgasms and then until Derek lost control of his bladder.

“Such great stamina,” Ennis said with pride. Noticing the stutter of Boyd’s hips at last as the stud picked up his pace again, chasing his climax, he added, “Looks likes Boyd’s finally shooting his wad. Good thing too, because at the way he’s emptied your boy, Derek’s dick was like to start spitting dust soon, he’s been fucked so dry.”

Both Alphas laughed at this and continued to exchange joking quips on Boyd’s virility and Derek’s fucked out state until Boyd finally pulled out. Ennis gathered up Boyd’s reins and  looked on while Deucalion videoed himself scooping up the pink-tinged cum leaking from Derek’s yawning gape.

“Boyd popped that ass-cherry good, didn’t he.”

Deucalion nodded as he fed the bloody cum back into Derek’s ass with four fingers before stoppering it up with the tail plug. He sent the video on to the twins and clicked off his phone. “Good thing his healing isn’t too arrested under the potions we’ve administered.” He whistled lightly at how loosely the plug rattled in Derek’s blown out asshole. “This thing barely catches the sides of his cunt now.”

Ennis clapped Boyd cheerfully on his shoulders in praise before leading his pony into the creek for a refreshing cold water rub down. After this, he hitched him back up to his buggy while Deucalion was still waiting for Derek’s ass to re-tighten enough to ensure his tail wouldn’t fall out on their journey back to the ranch.

When Deucalion finally loosed Derek from his stone hitching post, the pony stumbled back and all but collapsed in his arms.

“Doesn’t look like he’s gonna be up to pulling that cart home… but maybe a dip in the creek would revive him,” Ennis suggested.

Deucalion shook his head. “Maybe. But I’m not of the mind to have Derek forget his first ride too quickly, I’d rather take him home dirty. Let him think about it...” He walked the unsteady pony to his own cart and hitched Derek into it, though Derek sank to his knees as soon Deucalion’s hands left him.

“Why don’t you head on back, let the twins know what to expect. I’ll follow on after. Though if they watch that clip they’ll know already.” Deucalion added watching Derek clumsily fight his way back up onto his feet. “As you said before, this stud’s got a lot of spirit. It’s gonna take more than a few hard rides to really tame him.”

In the end, seeing the truth in the older alpha’s words, rather than head back, Ennis lingered. It was a long slow walk home but neither Alpha minded the slow pace, knowing that each labored step served to remind their new pony of his place.

* * *

 

Arriving back at the ranch they found Ethan and Theo rubbing down Theo’s Tandem team outside of the main corral.

“Scotts looking good there. Filling out nice,” Ennis hailed as his cart drew up.

The ponies Scott and Isaac had their heads down and eyes closed with exhaustion while they were being groomed, but these popped up at hearing the carts approaching. Both studs began whinnying frantically calling out to the new arrivals.

Theo quickly quieted Scott, forcing his halter-gag into his mouth and snapping it secure. Ethan went to do the same, but Isaac shut up and shied the second the Alpha reached for his head.

“I see Isaac is still spooky,” Deucalion parked his cart and stepped out to unhitch his steed. Derek had his head down clearly trying to avoid looking at the other ponies he’d come to the ranch with.

“Head shy for sure, but he’ll get over it eventually,” Ethan assured, picking up Derek’s reins and leading him over to a free hitching post.

Ennis freed Boyd from his cart. “Where’s Aiden?”

Theo snickered, “In the barn with the mare. That video the boss sent really riled him up.”

Hearing this the tandem ponies became wild, wickering and tossing their heads. It was only when they saw Ethan tie Derek off to head their way and Theo reach for the belted pouch at his waist that held his training aids, ginger root, clamps, and barbed cock cages, that they finally settled back down.

They continued to stamp in agitation though, glancing over at Boyd with expressions of nervous expectancy. The dark pony, however, remained non-plussed, too intent on rubbing his brow on Ennis’s sleeve in petition of having his itching bridle removed.

It was amazing the difference a few months training made in a pony. Ennis edged his fingers under the strap of Boyd’s headstall rewarding him for his good behavior.

“Why don’t you put the dynamic duo away?” He offered this more as advice than question. “Since this is the first time your pair have seen Boyd since they were brought in. Over-doing the reintroductions is just going to stir them up more.”

Quite the fan of chaos, Theo grumbled a bit but did as he was told. He’d been put in charge of Scott and Isaac because their personalities had deemed them the easiest to be tamed. And as the youngest hand on the ranch, he didn’t want to lose his privileged two pony spot.

Ennis hitched Boyd to the post vacated by Scott and began to take off his tack at last. Deucalion, meanwhile stood aside and let Ethan tend to Derek. Ennis clipped the heavy tie-out chain to the thick runed collar around Boyd’s neck before sliding the bit out of his mouth and hanging his bridle up.

He wiped Boyd’s face carefully with fresh cloths dipped in the bucket of clean, warm water left over from Scott and Isaac’s rubdowns. He washed and dried Boyd’s muscular arms too before loosing them from his harness, ensuring the skin was fully dry so he could slide them into the waiting arm binders their ponies wore at all times when they weren’t being worked with.

“Fuck, look at that!” Across from them, Ethan had just pulled the plug from Derek’s ass and a glut of cum had plopped out with it.

“I thought it looked amazing in the video, but damn, Boyd broke that ass like nobody’s business.” He ran his fingers around a rim so puffed it almost looked prolapsed.

Derek didn’t exhibit a whole lot of response to this fingering, however, in fact, he’d remained remarkably quiet since seeing the other new ponies and he continued to be subdued, even when Ethan fed the hose into his ass to clean him out.

“You want to leave the cock weight on him?” Ethan called out, giving the dangling ball a tap with his boot while one hand held the hose and the other rubbed Derek’s swelling belly.

Deucalion had left it on Derek after his rides knowing as slow as the walk home was going to be the weight wouldn’t do too much damage. That and with each weighted step back to the ranch it would be just another reminder that every part of the pony belonged to his riders.

“Yeah, Leave that on for the night. Might make him a little easier to catch in the morning.

“And make sure to scrub him good, and balm him, inside and out. I think Boyd did a little damage and I want Derek up and ready to be ridden by morning.” Deucalion had just finished saying this when Theo and Aiden emerged from the barn, both wearing wide grins.

“Aiden, I know how much you like the mares, but I expect you to start riding Derek too, every day. I want both of you mounting him as much as possible now he’s had his first ride. You too, Theo.

“He might look gentled now, but don’t let that fool you. I think this stallion is going to be particularly stubborn.”

“Sure thing, Boss,” Aiden grinned stepping up to his brother. “Mare, stud, it doesn’t make much difference, I’m always just happy to ride.”

Deucalion nodded, pleased to hear this and returned to watching Ethan attend to Derek’s battered bottom. Still flushed with bruise and whip-mark welts, the pony’s cheeks twitched and jiggled as Ethan went wrist deep into Derek’s freshly flushed out asshole to apply the ordered salve.

The head Alpha’s attention was pulled from this, however, by the crunch of gravel as a pickup pulling a trailer trundled up the main ranch road and stopped there at the corral.

Though he recognized the truck Deucalion was surprised to see it again so soon. He moved over from the ponies to greet the driver.

“Kraven, didn’t expect to see you again until after the next auction.”

A lean figure climbed out of the truck’s cab. “Yeah, I didn’t expect to be back so quick either.” Kraven ran his fingers through his longish dark hair sweeping it back.

“But my posse and I have found ourselves in a bit of a situation, and I thought we might be able to help each other out.”

“Oh?” Deucalion arched his brow, intrigued.

“Yeah…” The two of them walked around to the back of the trailer and Kraven opened it up. He disappeared into the darkness and emerged a moment later leading a handsome caramel-skinned pony with wild eyes and with clearly a lot of fight still in him.

“That blogger kid that tipped us off to those last loose-pack ponies you bought up. Well, him and this one caught on to us. Tracked us down trying to get their friends and the blogger, Stilinski’s, boyfriend back. Thought they were being sneaky too, the little shits.

“Anyway, we caught em. But one of my werewolf hands kind of lost it the fracas, and well… He bit this one. So, what you have here is fresh-turned wolf, as well as an unbroke pony.

“You know how strict the rules are these days about turning… anybody finds out about this, we’ll lose our wrangling license.”

Deucalion nodded, understanding the seriousness of Kraven’s situation. “Why not just kill him?”

Kraven shrugged his head and grinned. “Well, cause dead weres don’t bring much profit. Now he’s not registered, but I figured, knowing how much you and your crew like a challenge and because you tend to find rules somewhat flexible, the same way I do, at times,… Well…  I thought we might be able to come to some sort of agreement.”

“I want him!”

That was Ethan who had just pulled his hand roughly out of Derek’s ass and made his way over. His eyes drinking in every detail of Kraven’s caramel pony.

“Hoped you might say that,” Kraven grinned. “I’ve already pulled his teeth for the bit and did the voice alterations. But you can do the rest of the details. If you buy him, I’ll help you snip his cock and brand him before I go, if you want.

“I’ve even got a little bonus in the back I’ll throw in if we can come to an agreement.”

Ethan looked at Deucalion, his expression all but begging.

“Show me the bonus and then we can talk some numbers,” Deucalion grumbled, not that he didn’t want the new pony but he sure wasn’t about to show such blatant interest to the wrangler. No need to pay more than he had to.

Kraven handed the fresh pony’s lead to Ethan. “They called him Danny, “ he offered before ushering Deucalion into the trailer to see just what he planned to sweeten the pot with.

* * *

 

An hour later, after all the interruptions and the commotion, Aiden led Derek into his isolated stall at the far end of the Alpha pack’s huge stable. The stallion was clearly exhausted but clean and wearing his off-training tack.

“Boss thought you might be getting a little lonely out here all by yourself, so he got a barn buddy for you today.” Aiden clicked a latch and slid back the stall’s wood-paneled wall to reveal the bars between them, allowing Derek to see into the other cell.

He whinnied and tried to pull away when he saw the stall’s contents but he had little success the way he was bound. His arms were behind him in a sleek corseted fabric binder that pushed his muscled chest out, his feet laced up in the breathable night splints holding them in the proper confirmation for his absent boots.

“Kraven gave him as a freebie with Danny. Course, we can’t use him for cartwork, humans, even sparked ones, just don’t have the stamina. But Alpha’s been wanting a dog for a long time. He’s not just a horse lover, you know.”

Aiden tied Derek’s lead to the bars facing into the other stall and fumbled with the new plug he wore with its shorter tail for nightwear. “Bet all that salve has you nice and slick, huh? You know Deuc did say you should be ridden as often as possible. Sore as you gotta be, you’ll probably clench a lot.

“I fucking love that.”

Derek’s next whinny sounded more like a whimper and he tried again to pull away, but Aiden stopped this with a few quiet words.

“Easy boy. Let me take a quick ride and then I’ll leave you to get re-acquainted with your new stablemate. Otherwise, if I have too much energy, I might decide to spend the last part of my day playing with Alpha’s new puppy instead.

“Don’t know if you’re the jealous type. Kraven said you two used to be a thing.”

Aiden grinned when Derek immediately settled. “Perfect. You made the right choice, stud.”

He slid the plug out from between Derek’s cheeks and his cock in, pressing Derek forward until the pony’s puffed pecs were smashed against the bars.

“Boss is calling his new puppy ‘Sparkles’,” Aiden huffed as he started pumping into Derek’s salve-slick hole. “He doesn’t usually change his stock’s names but he said the pup’s last one was too long and his first one was too stupid.”

Outside his ragged breathing, Derek made no sounds in response to his trainer’s goads; he didn’t offer any further struggle either. He just stood there, the weight still on his cock swinging like a pendulum, clinking against the stalls bars as Aiden exacted a fast, hard-riding fuck on his still bruised and battered ass.

The Alpha came quickly and stuffed the plug back into Derek’s ravaged hole as soon as he pulled out his dick stoppering his cum up inside.

“Good boy…” Aiden unclipped the lead to Derek’s stall halter, this headgear wasn’t as aggressive as his bridle but still left him lightly gagged for the night. “There you go, Derek.”

As soon as the lead was released, Derek dropped down and crawled over to the blanket covered pallet, the only soft place in his straw-filled cell.  Aiden watched the pony turn his back on both him and the other stall’s occupant. He grinned over at Stiles who was shut up inside the stall in a smaller metal dog crate.

Stiles was muzzled with a dog bone-shaped gag, his hands encased in elbow length mittens,  and his ankles bound to thighs by a leather humbler. The rubber tail plug in his ass waggled happily as Stiles shifted in his cage but his eyes were swollen and bloodshot from crying.

“Looks like Derek doesn’t feel like being friendly right now, Sparkles.” Aiden slipped out of the stall and closed its lower half door. “He’s a stubborn steed like Boss says, but I’m sure he’ll warm back up to you eventually.

“Not that there’s any real hurry: you two have all the time in the world now to get yourselves figured out now.”

**Notes for the Chapter:**

> Hope you enjoyed that ride as much as I did. 
> 
> Thanks for stopping by.
> 
> *costumes*  
> Derek and the pack - ponies  
> Alpha Pack - cowboys  
> Stiles - puppy

**Author's Note:**

> Appreciate you dropping by. Don't forget to say "thank you" for the sweets, kids.


End file.
